Dyeings fast to light



Patented July 23, 1940 UNITED STATES 7 Dramas ms'r T LIGHT Hanna Rein, Bad Homburg vor der Hohe, Germany, assignor to I. G. Farbenindustrie' Aktlengesellschaft, Frankfort on the Main,

.Germany,

No Drawing. Application March 22, 1939, Serial No. 263,402. 'In Germany March 24, 1938 6 Claims.

The present invention relates to dyeings and it especially relates to dyeings fast to light. It is an object of the present invention to produce dyeings fast to light on fibers which have been made capable of adsorbing wool dyestuils.

As is well known, dyeings obtained by dyeing with the usual wool dyestufls animalized materials of natural or artificial origin, especially fibrous materials from cellulose or cellulose derivatives exhibit in most cases an essentially decreased fastness to light compared with the dyeings obtained with the same dyestufis on wool. According to the kind of fiber, dyestufi and animalizing agent, these difierences in the fastness to light may be very great; thus, it occurs sometimes that dyestuffs which, as such, display a very good fastness-to light, when applied to animalized fibers which have been rendered capable of adsorbing acid wool dyestufi's, for instance by introduction of nitrogen-, sulfuror phosphoruscontaining compounds, yield dyeings the fastness to light of which is too small for practical use.

Now I have found that the fastness to light of such dyeings may considerably be enhanced by incorporating with the animalized artificial or 25 natural materials non-basic organic compounds of about -30 carbon atoms containingsulfuric acid radicals. Sulfonic acids of poly-halogenopoly-hydroxy triphenyl-methanes, for instance, have proved to be especially suitable. As artificial or natural materials there may be used above all fibers, ribbons, films and layers from regenerated cellulose, cellulose derivatives, cotton, fiax, hemp, ramie and jute. The procedure may be as follows: Either the finished dyeing is subjected 35 to the action of the products containing the sulfuric acid radicals, or the after-treatment is effected in the dyeing bath or also the animalized materials are treated before dyeing. The reaction may be performed at ordinary or elevated 40 temperature. It is,-furthermore, possible to add to the spinning solutionor to the spinning or after-treating' baths the sulfonation product and the animalizing agent or the product'of reaction obtained from both agents.

Viscose fibers which have been prepared by the process of U. S..Patent 2,065,175 and which have i been animalized by incorporating with the spinning solution 4% of the condensation product w from trichlorinated hard paramn and poly-ethyl- In many cases, the present process effects, at

ene-polyamine are dyed, in the presence of wool, with'2% of the following dyestuffs:

naphthylamine-3.6-disullonic acid benzidine phenol, condensed with perawtoluene-suliochloride I 1.4-diamino-3-phenoxy-anthraquinone-2-sulfonic acid (of. German Patent N0. 563,201) diethyl-benzyl-diamino-diphenyl-methane-disulfonic acid (of. Schultz, l. c. 806) It results that the dyeings obtained onthe animalized cellulose fiber display a considerably smaller fastness to light than the corresponding dyeings on wool. If, however, the dyeings produced on the animalized fiber or on a mixed fabric from animalized fiber and wool are treated in a rinsing bath containing per liter 0.6 g. of 3.5'.3".5' tetrachloro 2.2' '-dihydroxy-triphenyl-methane-Z-sulfonic acid and 0.2 cc. of acetic acid of per cent strength, they become as'fast to light as those produced on wool; a levelling efiect is in most cases produced atthe same time.

Example 2 Cuprammonium fiber is animalized by incorporating with the spinning solution 3% of the condensation product named in Example 1 and treated in the acid spinning bath with low content of acid, with 2 g. per liter of 4.3'.5'.-3".5"-

penta chloro 2'2"-dihydroxytriphenyl-methane-2-sulfonic acid. Instead of adding the sulionic acid to the acid spinning bath, the fibrous material may also be treated, after washing, with a solution of 2 g. per liter of the above sulfonic acid, a small amount of acetic acid being added.

The material thus treated is then dyed with 1% of the dyestuif para-amino-benzoyl-ethyl-alphanaphthylamine- 1-benzoylamin0-8-naphthol-i.6- disulfonic acid (cf. German Patent No. 269,213) a dyeing is thus obtained which displays a considerably better fastness to light than the dyeing obtained on a fiber not subjected to the said pretreatment. The same result is obtained if the equal parts of wool Example 3 Fibers which have been animalized'by means (2) The dyestufl. obtained by condensation of para-chloro-benzaldehyde with ethylbenzyl-meta-toluidine, trisulionation, ox-' idation and melting with para-phenetidine (ct. German Patents Nos. 293,852 1 6 of the product obtained by the action or carbon d 287,003) (B) disulilde upon poly-ethylene-imine are dyed with the dyestufl mentioned in Example 2. The dyed p y ee'i-t-d su fon c acid material is'then after-treated in'a rinsing bath Bemmme containing 0.6 g. per liter of the .tetrachloro-di- 10 hydroxy-triphenyl-methane-sulionic acid named phenoloondemd with mwluemmwmoflde in a p 1 and a eti a d- Th dyeing thus (cf. German Patent No. 261,047) (C) obtained is considerably faster to light than'with 4 Th dyestufl prepared from anisaldeout the Said treatment hyde, ethylbenzyl-aniline-sulfonic acid 1 Example 4 and para-phenetidine according to the rocess oi Exam 1e 5 of German Patent Cellulose fibers are pre-treated with the con 3; 293352;v p I (D) densation product from ethylene-imine and oc- (5) 4 amin 3 methy1 h e x a n y d r O V todecyl-bromide and then dyed with one Of the f t 1 1 1 Gelv v wool dyestufis mentioned in the preceding examman Patent 533,617) (E) 20 5- The dyeing thus tamed is in a (6) H-acid l.8-naphthylamino-sulfonic rinsing bath, acidified with acetic acid, and conacid (F) taining per liter 1 g. of the bis-(l.2-dich1oroben- (7) -zenei-sulfonyl-3-aminobenzene-l'-sulfonyl-3"- .th1 suuomc acid (eff Geman Patent anunobenzene-l"-sulion yl) -diamino-stilbene-di- 330,594) i (G) I sulionic acid named in German Patent No. a sodium 1.4 d1am1n 2 phenoxy an 544,976. A considerable improvement of the fastthraqumne 3 su1fnate (on German ness to light is thus ObtBilld. Patent No. 5 3201 I (H) E l 5 I (9) Primulin-sulfonic acidphenyl-gamw) Viscose artificial silk is animalized by adding ma'md t (I) (10) Aniline 2-chloro-acetylamino-5- to the viscose spinning solution, shortly before u hthol 7 suu m cm German the spinning process, the product obtained by nt 557 c (K) o the action of 3'.5'-3".5"-tetrachloro-2'.2"-dig f 3 I hydroxy-triphenyl-methane-2-sulionic acid upon Ionic a M d 2 mo'ls of aetmac'etic acid 35 the condensation product from trichlorinated anmde and dystufls' (L) hard paraflin and polyethylene-polyamine; the (12) Anmne (2 mols) material thus obtained is then dyed, in themanmphm1c acid 6, su1fn am i n ner usually applied in wool dyeing, in a neutral 8- naphth1 4 edisulfomcyackfmf bath with the dyestufl No. 864 (Schultz, l. c.) or

40 man Patent No. 274,082) (M) 40 1 with the dyestufl No. 785 (Schultz, l. 0.). The (13) A mixture of and 01m din rtho fastness to light of the dyeings thusobtained is sulfanmdee hen 1 practically the same as that of the wool, which ymzolone (c! f Patent No 3 has been dyed simultaneously, the tinctorial 2 239) and rwtolmdmemrthmsul: strength being, surprizingly, in better conformity 4. fanilide 1.4-naphthol-sulionic acid (cf. 4.,

with that of the wool than,is the strength of a German Patent No 230 594) and the dyeing'pmduced ammanzedfiber tamed stuffs Nos. 1199 and 1200 (Schultz; 1. 0.). .(N) as usual without the addition of the above product. (14) A mixture or The following table indicates a certain numm in numb) anthra umone 2 i 3 her of further examples which illustrate the procq fonic acid (cf. German Patent No. 00 -ess of the present invention. The following dye- 280646) and orthmamm o1 lsulfone stufl's have been used: i y (1) Para-amino-benzoyl-e t h 37 l-a l p h ae i... p t u o c ac d naphthylamine benzoyl-K-acid (ci'. v and sulfor ated 3-hyd y- -q Dh- German Patent No. 269,213) (A) thalone (cf. French Patent No. 775,935) (0) I I Treating Animaiizing agent Dyestui! Treating agent Treating manner teitngam- 6U I Degrees 1 Reaction product from trichlorohard- 2%oidyestuflA 3'5'3"5"-tetrachioro-22"- Treatment aiterdyeing 20 parafllne and polyethylene-poiyadihydroxy ti'i henyl i mine. mgt hane 2-sulion cacid. an 20 4 27 old estufi 2 do "'fie t nent before d i'n g 3 gggy sm:g 33" Trea t nientaiterdyeingnn. g3 65 2% of d estm! Nr. 61 0 d0 20 (Sch tz,l.c.). 2%oicyestufl E- do .....do 20 d0 of F do r0 2) ofcyestnfl 6..-..- ..do m 2) d 2%0feycst H in w %332%i :2 2: t a 7 1 "I 0.6% ofdyestufl it Tr%atm e nthi1mmediately 20 i 15 e. 'd0 2%ofdyestuflD Seem-.1. T?e%i ii ?ite%dyein 60 U16 Pentachlorohard-parafilne and poly- 2%0! dyestufll) do do l7 r ii t 'e fiit f i ggmhine and eth 2701a than I do do 10o (B l nediami'ne. t y I G u V I A lreating Animai fl a agent Dyaetnfl' Treating agent Treating manner mllupleola' Dogma B Polycthyleneimin 2% o! dycetufl D See Nr. 1 Treatment alter dyeing..---- 100 D TrlchIorohard-parafllne and poly- 2% dyastul! D do do ethylene-polyamine treated with dimethylsuifate. 1 0 Carbon disulflde and polyethylene- 2%0! dyestuflD do do 100 imine. ll Octodecylbromide and ethylcnel- 2% 0i dyestnl! D -do 100 mine. a 4 :2 Reaction product from trichlorohard- 1% of dyestnfl A do Treatment before spinning parafline and polyethylene-polyamine treated with 3 5' 3" 5-Tetrachloro-2' 2"-dihydroxy-triphenylmethane-z-sulionic acid. Z5 d0 2%016, M. o .do 24 Mixedyarn consisting of 50% wool and 1.6% o! dyestufl! N. do Treatment alter dyeing %matenalaspe1-Nos. 1-15. 26 .do -1 0.75% o! dyestufl 0.. do do 20 I claim: 4. The process of improving the iastness to light of dyeings obtained textile materials by means which comprises inco contains a polyhalogen- 1. The process of improving the tastness to on animalized fibrous of wool dyestufls rporating in these materials polyhalogen-polyhydroxy-triphenalmethanesulfuric acid.

2. An animalized flbrousa textile material; which methane-sulfuric acid.

3. The process of improving the fastness to light of dyeings obtaine textile materials by means 0 which comprises incorporati 3', 5', ii,v 5"-tetrachloro,-2,

p yhydroxy-triphenyld on animalized fibrous f wool dyestuilfs ng inthese materials 2"-dihydroxy-triphenyl-methane-Z-sulioni'c acid.

light of d'yeings obtained on animalized fibrous textile:= materials by means of wool dyestufls HAlflNS 1mm. 

